Curable monomers comprising a polyalicyclic structure element are substantially known and are used in numerous applications, such as dental engineering.
Within the context of the present text (meth)acrylic means both acrylic and methacrylic.
EP 1 238 993 describes a method for producing polyisocyanates containing acyl urea groups and mixtures of these and their use as starting components for the preparation of polyurethane synthetic materials.
DE 43 14 252 A1 (corresponding to U.S. Pat. No. 5,580,947) relates to a method for preparation of olefinically unsaturated isocyanates through reaction of isophorone diisocyanate and selected olefinically unsaturated carboxylic acids. The resultant olefinically unsaturated isocyanates are suitable for use as binding agents in coating materials.
U.S. Pat. No. 3,517,039 describes acylated urea polyisocyanates, prepared by reacting organic diisocyanates with organic monocarboxylic acids. The products described in U.S. Pat. No. 3,517,039 can be used for the preparation of heat-resistant foams or polyurethane elastomers as well as in particular elastified lacquer coatings.
EP 0 611 752 A1 discloses a method for preparation of olefinically unsaturated isocyanates comprising urethane groups while maintaining a certain NCO/OH equivalent ratio. The isocyanates that can be obtained according to EP 0 611 752 A1 can be used as binding agents for coating materials to be used at room temperature in single component form.
EP 0 209 700 A2, DE 35 22 006 and DE 35 22 005 describe (meth)acrylic acid derivatives of certain tricyclodecenes with divalent bridge members from the group of urethanes or ureas, which can be used in the area of dentistry.
EP 0 000 194 A1 (corresponding to U.S. Pat. No. 4,160,080) describes polyisocyanates, containing allophanate groups. These allophanate polyisocyanates may be used for the preparation of polyurethane foams, elastomers, duromers, coatings, adhesives and lacquers.
EP 0 682 012 B1 relates to a method for the preparation of bright-colored, light stable (cyclo-aliphatic) polyisocyanates comprising allophanate groups, by reacting organic compounds having urethane groups with organic polyisocyanates with (cyclo)aliphatically bonded isocyanate groups in the presence of tin(II) salts. The polyisocyanates described in EP 0 682 012 B1 can be used as synthesis components in the preparation of polyurethane synthetic materials.
EP 1 727 846 B1 discloses a method for preparation of binding agents containing allophanate groups, comprising groups reacting with ethylenically unsaturated compounds under polymerization under the effects of actinic radiation.
EP 0 712 840 B1 relates to a method for producing certain polyisocyanates comprising allophanate groups through the reaction of compounds comprising urethane groups with the formation of allophanate. The compounds according to EP 0 712 840 B1 can be used as binding agents or binding agent components in coating media.
EP 0 867 457 B1 discloses an ethylenically unsaturated polyurethane, which is substantially free from isocyanate groups, which is the reaction product of an ethylenically unsaturated polyisocyanate, containing allophanate groups and β,γ-ethylenically unsaturated ether groups, with a hydroxyfunctional, ethylenically unsaturated compound, wherein the ethylenically unsaturated polyisocyanate is prepared by allophantization of the urethane groups-containing reaction products of an organic diisocyanate with a β,γ-ethylenically unsaturated ether alcohol, wherein the β,γ-ethylenically unsaturated ether alcohol is selected from the group consisting of glycerin diallyl ether, trimethylolpropane diallyl ether and pentaerythritriallyl ether. The ethylenically unsaturated polyurethanes with allophanate groups disclosed in EP 0 867 457 B1 can be used as binding agents in single component coating compositions.
DE 10 2007 040 240 A1 and EP 1 645 582 A1 in each case describe a method for preparation of radiation-curing allophanates through the reaction of compounds containing isocyanate groups and hydroxyfunctional compounds, wherein the ratio of NCO groups to OH groups is 1.45:1.0 through 1.1:1.0. According to DE 10 2007 040 239 A1 with the use of certain mixtures containing hydroxyethylacrylate and hydroxypropylacrylate as the hydroxyfunctional compounds corresponding radiation-curing allophanates are obtained. The radiation-curing allophanates according to these three documents can be used for the preparation of coatings and lacquers, as well as adhesives, inks, casting resins, dental compounds, release agents, photoresists, stereolithography systems, resins for composites and sealants.
DE 10 2004 060 285 A1 relates to radiation-curable compounds based on a dicidol mixture (containing two or three isomers 3,8-, 4,8- and/or 5,8-bis(hydroxymethyl)tricyclo[5.2.1.02,6]decane) with at least one compound, having at least one ethylenically unsaturated grouping with simultaneously at least one reactive grouping in relation to dicidol, wherein this compound may be a reaction product of hydroxyalkyl(meth)acrylate and diisocyanate. The compositions according to DE 10 2004 060 285 A1 can be used as radiation-induced-curing coating materials, adhesives, laminations, printing and other inks, polishes, varnishes, pigment pastes, fillers, cosmetic materials, packaging materials and/or sealing and/or insulating materials.
WO 2006/063891 A1 discloses radically polymerizable compounds, substantially containing the reaction product of a dicidol mixture and at least one compound, which has at least one ethylenically unsaturated grouping with simultaneously at least one reactive grouping in relation to dicidol. The areas of application correspond to those mentioned in DE 10 2004 060 285 A1.
WO 03/035013 A1 and DE 602 16 951 T2 relate to dental adhesive compositions for bonding dental restoratives to dentin and/or enamel. In these documents, the preparation of 3,(4),8,(9)-Bis(2-propenamidomethyl)tricyclo[5.2.1.0]2,6-decan, amongst others, is described.
U.S. Pat. No. 6,670,499 B1 describes diurethanes derived from adamantane. The compounds described in U.S. Pat. No. 6,670,499 are suitable as intermediate products for use in dentistry or for producing optical materials (such as lenses, for example).
In the area of dental engineering and for various other application there is a constant need for further polymerizable monomers. There is in particular a need for monomers which allows the preparation of products and polymers with improved characteristics, for example an increased hydrophobia and/or a higher mechanical stability.